Waiting For Superman
by LiveLaughDreamInspire
Summary: Damon's at a low point in his life with Katherine's return to Mystic Falls and Elena's refusal to waver from Stefan. Caroline's newly turned with a fresh attitude and still trying to find her way. All it takes is a single conversation to change their lives forever. Damon/Caroline. Starts off at the beginning of season two.
1. The Turning Point

**A/N - It's been a while since I've written any fanfiction but I have been writing in my absence. This is my first Damon/Caroline multi-chapter story so I'm actually really excited about this story and pairing. This takes place beginning of season two. Caroline's just turned and Damon has just been told by his past love, Katherine, and his current one, Elena, that for both of them it will 'always be Stefan'.**

**This chapter is going to be really short compared to the rest of the story because it's the scene that sets the story. Everything is cannon from the show until this moment. It's the turning point in these two character's relationship**.

_**Disclaimer: I don't own The Vampire Diaries or any of these characters unless otherwise stated. No matter how much I wish I did.**_

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_ "It may be said with a degree of assurance that not everything that meets the eye is as it appears."_

_-Rod Serling_

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Caroline wasn't sure why she was here. Sitting alone at a booth in the corner of the grill. She supposed it was because she had no where else left to go. Life seemed to be falling to pieces around her and she couldn't figure out a way to put it all back together again. Over the course of a couple weeks her life had made a complete one-eighty and she just wished she had someone to go too.

She had just finished spending the day hunting little rabbits with Stefan, and although he was trying his best, it was just difficult to learn control from someone who couldn't manage it over himself.

Caroline liked Stefan. Not in the wanting to be with him sense, or even the wanting to fall in bed with him way, but just as an overall person. He was like the big brother she never had but always wanted. It's been close to two weeks since she's become a vampire and he was the only one who immediately offered to help her. Despite how much she knew he didn't like her beforehand. And that meant something to her.

Caroline wasn't naive. She knew that she was the last person any of them wanted to have mixed up in this supernatural drama. Selfish and shallow and only caring about her image. She was the little blonde cheerleader no one could get close too and no one really wanted to spend time with. She didn't particularly mind that though. Sure, she hated to be alone but that was infinitely better than being around a bunch of people who were indifferent to her existence.

That's why she liked Stefan. He's been the first person who's been real with her in a very long time. Well him and Matt, but she couldn't be around Matt right now so she had to focus her attention on something else. Anything but dealing with her own issues. So she's decided that she was going to take this Salvatore friendship seriously. It's been an awfully long time since she's let anyone in for _real_. Hell, it's been a long time since someone's even tried. But she was going to need the help if she was going to survive in this world. Perseverance. It was critical. She had discovered this at a very young age.

It was this mindset that compelled Caroline to get out of her lonely little booth and make her way across the bar towards the eldest Salvatore brother. Damon and her had a complicated past to put it mildly, he fed on her and used her and then tried to kill her, and she remembered every vivid detail. They weren't on the best of terms right now, but he was seated at the bar when she came in over an hour ago and she lost count of how many drinks she's already seen him shoot back and who knows how many were before she arrived. It may not have been any of her business but while she and Stefan were talking today it dawned on her how much he really needed his brother. Even if he was a manipulative asshole. She just wanted to help.

"Well, don't you look cheery." Caroline greeted as she slid into the bar stool beside him, absentmindedly raising her hand so the bartender would notice her on his next round. This was a lie of course. Damon looked anything _but_ cheery. In fact, he looked like someone dragged his heart around through the dirt and ran over it with a semi, but she wasn't exactly going to show him any form of sympathy.

Caroline heard him exhale although she wasn't looking in his direction. It was heavy in irritation and she couldn't help but smirk at the realization that she was annoying him. _Good_.

"Is this the game plan? I hurt you so now you're going to annoy me for the rest of eternity? Hardly seems like a fair trade." His tone was mocking as he finished off the contents of the glass in his hand. Caroline wasn't an idiot. She knew he didn't care about a thing he did to her. It was now just an inconvenience that she regained her knowledge of the whole series of events.

"Yeah, you know, I was sitting around today thinking to myself; 'Self, what's the best way to get back at Damon for all the shit he's done?'" Tilting her head, she glanced in his direction and she could have sworn she saw his lips twitch. But she could have been wrong. "And then it came to me - annoy him until he felt he had no choice but to stake himself. It's perfect."

Grinning to herself, she ordered a rum and coke when the bartender came back, watching as Damon gestured down to his now empty glass in a silent command for another.

"I have to give it to you, Blondie. That plan might actually be fool proof. You do have a nasty little habit of being the most annoying thing that walks into a room." Now she knew she did see the edge of his mouth twist upwards. The bastard was _smirking_ at her. Caroline wasn't fazed though. She was used to it. It sudden became very obvious to her that this wasn't just a random drink at the bar to avoid his brother or whatever. He was hurting over something - and he was taking it out on her. And here she thought they might have moved past this.

"And you have a habit of being the most obnoxious but you don't hear me complaining." Shrugging her shoulders, she smiled gratefully as the blonde haired man delivered her drink. He's been the bartender for the past month and one of her first acts of vampirism was compelling him to serve her without hesitation. Caroline had to admit that the whole being dead thing had some perks. She caught Damon's head turning in her direction as she glanced back at him, raising a brow as he gave her a look of disbelief.

"You never shut up about it!" His tone rose slightly in volume as he held his glass outstretched in front of him in a gesture that conveyed that he couldn't believe she was suggesting anything otherwise.

"You're right. I never was good at filtering." A smile overtook her features as he continued to just stare at her. As if he really was at a loss for words. "So how about since we're both the most annoying things on the face of the earth and currently drinking alone, you tell me what your problem is. I won't guarantee that I'll care, but I could use the entertainment."

"Shouldn't you be out with Saint Stefan lowering the town's animal population one squirrel at a time?" No smile. Just a heavy resentment that Caroline couldn't ever imagine feeling towards a sibling. Weren't they supposed to like... love each other unconditionally or something incredibly cheesy like that? She wasn't exactly sure how the whole sibling thing worked. But personally, she couldn't imagine losing one over a girl. It seemed to always come down to one with these two.

"Already did that and I'm scarred for life. But I'm not the one drinking my problems away."

"You're not adapting to the Stefan diet well? Shocking." Damon responds sarcastically, clearly avoiding her questioning. Caroline was pretty sure he's thinking about how he's still right on what kind of food Stefan really needs. She remembers him mentioning it a few times to her in privacy during one of his venting sessions.

"Wow, you're bashing on your brother. Must be Tuesday." She has to roll her eyes. It's just ridiculous. All this sibling rivalry. Caroline's grown up with Elena and has been friends with her for a very long time and although she thinks of her as a somewhat good person, she doesn't think Elena is worth tearing apart a family.

"Well by all means, if another member of the Stefan fanclub has something to say don't let me stop you. It's _always_ going to be Stefan, right?" The bitterness was obvious in his tone as she watched him finish yet another drink. That was about when she decided she's had enough of this.

"Would you shut up? My god, you're turning _into_ the brother you claim to hate so much with all this brooding." That seemed to catch his attention. Damon's head snapped towards her so fast that she's surprised he didn't just give himself whiplash. "Let me guess, Elena turned down another one of your numerous advances and now you're drowning yourself in your own self pity. But let me ask you something; have you ever thought about what you were going to do after you got the girl?" This seemed to have stumped him as his gaze dropped down to his glass before he sneered in her direction.

"Have you ever thought about how no one would care if I ripped your heart from your chest right now?"

"Think about it, Damon." Caroline snapped, her teeth gritting together. Somehow he could still manage to create a blow, no matter how many times she told herself that she wouldn't give him the satisfaction of being able to hurt her anymore. "Lets say you manage to steal Elena out from under Stefan. Then what? Could you live with knowing you stole away his main source of happiness? I mean, maybe you do love her more. Maybe he'll move on and years later he'll find someone new." There was something in his gaze, like a twinkling of hope that she might be right and Caroline almost felt horrible for the next words that were about to come out of her mouth. Almost. "But he'd never forgive you. Regardless of if he manages to move on or not. So instead of hating Stefan and punishing him because Elena loves him. Maybe you should ask yourself if she's worth _losing_ him."

She probably could have toned down the bite in her voice but she was growing disgusted by the entire situation to begin with. So with that, Caroline hopped back off the stool and took off towards the front door. Leaving the raven haired man behind to stare after her. Pondering over both the words and the mysterious young woman he was beginning to realize he didn't know in the slightest.

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**A/N - Reviews would be appreciated on whether or not I should continue. They really do fuel inspiration.**


	2. Memory Lane

**A/N - Hey guys. So this one is significantly longer than the first. It takes place over the course of episode 2.4. 'Memory Lanes'. As the story develops it's going to break off more from the original plot of the show. Hope you all enjoy it. Also thank you so much for the reviews/follows & faves!**

**Disclaimer: I don't own TVD or any of the plots that go along with it, I just like to play around with them. **

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_Caution: Objects in mirror are more fucked up than they appear_.

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"Fuck, fuck, fuck, fuck, fuck." Caroline repeated over and over to herself as she sat perched on the edge of her bed, fingers weaving through unruly blonde hair as she tried to come up with a way to get herself out of this mess.

Katherine had just left and now she was forced to report on Stefan and Elena's relationship and try to discourage Elena from perusing it further. How was she supposed to accomplish that? Elena and Stefan loved each other and Elena sure as hell didn't care enough about her opinion to put a stop to anything. But if she didn't do it then not only would she be killed but so would everyone else she cared about and Caroline wasn't about to let _that_ happen.

Drawing in a deep breath she allowed herself the standard thirty seconds of freak out. It was something she developed and perfected as a child. Get overwhelmed by the situation, take another breath, analyze the problem from every angle possible, breathe again, find a solution. She could do this.

Once she maxed out on her 'freak out' time, she didn't bother to try and wipe the tears from her eyes as she began thinking over the problem. Why was Katherine so interested in breaking them up in the first place? There had to be a reason. Unless it was purely for her own entertainment, which Caroline wouldn't exactly put passed her.

She took another deep breath.

They had to go through with it. It was like what mom always said about killers and hostages. You went along with whatever they wanted until you could take them out without putting any of the civilians in danger. They needed to get rid of Katherine and the easiest way to do that would be to play along. Let the older vampires guard drop, let her think that everything's going the way she wants it, and then take her by surprise.

Rising to a stand, Caroline crossed the floor to her vanity dresser and eyed herself in the mirror. She covered the dried tear tracks in a coat of foundation and followed it up with a swipe of lipstick. Pursing her lips she gave a quick nod of approval. There was a job to be done and she had to make sure the two love birds followed through. Putting a pause to their relationship for a short while until they could kill the wicked bitch of the west off seemed like a much better sacrifice than the lives of many. They'd live.

A grin grew on her features as she headed out her bedroom door and down the stairs. Caroline had a plan and it was always a good day when she could dedicate her time and energy into a single task.

~§~

"Was that Stefan?" Caroline asked innocently as she took a seat across from Elena on the front porch of the Gilbert-sted. She, of course, already knew it was and she also already knew that the reason Stefan wasn't here was because he was currently tied up with Katherine. She sent a silent prayer out to her friend but she didn't allow herself to worry too much. Stefan could take care of himself and right now she had to start putting this plan in motion.

"Yeah, he hasn't called me back. I'm trying to decide if I should be worried." Caroline could sense the worry in Elena's voice and nervously ate a chip out of the bowl on her lap. She couldn't let emotions get in the way of this. She knew that but... It didn't make hurting her friend any easier. She needed a tactic, she decided as she started rambling off about hunger.

"Its horrible, you know? Having to constantly fight off the urge for blood every minute of every day..." As they spoke, Caroline could see the beginning form of doubt growing in Elena's mind and she desperately hoped that she wouldn't lose her or Stefan over this.

Luckily enough, Alaric broke up the moment with his sudden appearance and if she could, Caroline would have let out a sigh of relief. Plus, she really was starving. In a way she was only speaking the truth to Elena. It was a harsh, black and white one. But every piece of it was true. After all, she couldn't be with the guy who actually loved her because of it.

But she also knew that fighting the urge was both worth it and a capable thing in Stefan and Elena's relationship. They were each others 'soulmates' or whatever. She had no doubts that at the end of this and whatever conflict that arose afterwards, they'd find their way back to each other.

"Ooh. I see shot glasses. Did I miss all the fun?" Caroline greeted as she stood beside Mason at the kitchen counter. Ignoring Damon's gaze on her, she knew he had to have heard her and Elena's conversation out on the porch. She had to act natural. There's no reason to believe she would have another motive behind her words since they were entirely laced in honesty.

"I don't think you're legal yet, baby Forbes." Feeling an arm drape around her shoulder, she glanced up to shoot Mason a grin. She used to have such the crush on him growing up. It was why she spent an excessive amount of time at Tyler's house during middle school.

"Never seemed to stop you before..." Trailing off, she stole what she guessed was his shot glass from the kitchen counter and reached for the already half empty bottle.

"You two know each other?" It was Alaric who spoke this, surprised by the friendlyness between the two. He'd yet to see anyone display that sort of easefulness around the young blonde and until this moment he never questioned why.

"Its a small town, Ric. If I were you, I'd be concerned if we didn't know each other." Shrugging her shoulders absentmindedly, she immediately filled the tiny glass and shot the contents back, relishing in the burn it left trailing down her throat.

"Caroline used to hang out with Tyler a lot when they were in middle school so since she was always around I used to drag the little brat with me for surfing contests and to work when I was a mechanic in town." Mason explained to what seemed to be very shocked faces on everyone except Jenna. Who knew because when her and Elena were in middle school Jenna was still living in town and dating Logan. Which always annoyed Mason so in turn, it annoyed her when she had to hear about it.

"My god, remember when you decided to get her drunk on her thirteenth birthday? I still can't believe you dragged me into that." Jenna laughed, shaking her head at the memory. Oh yeah, aunt Jenna was most definitely a little tipsy.

"Dragged you into it? I seem to remember you offering your assistance! Besides, I was teaching her a valuable lesson. She probably couldn't even look at alcohol for years after that hang over."

"Actually, I made it until Halloween but close enough." Caroline interrupted, not exactly thrilled with this trip down memory lane. She put a lot of effort into making sure that person was buried behind the one she put up at the beginning of high school.

"And I only offered to help so Liz wouldn't shoot your dumb ass. I wasted a perfectly good date night running around and hiding the sheriff's daughter."

"It was scum Fell though, Jenna. I think you were just looking for an excuse to avoid his bed for the night." Scoffing a laugh into the empty glass, Caroline sat it back on the counter and elbowed Mason.

"Be nice. It's not her fault that you're still not able to find someone who'll put up with you." High-fiving Jenna when the older lady leaned over the counter, she turned smugly in his direction as though waiting for some form of a comeback. Her smile faltered when she caught the hardness in his gaze, maybe he had found someone after all? But then why was he keeping it a secret?

"So, I'm thinking pictionary. Who's in?" Hearing Damon's voice, Caroline looked around Mason to get a good view of him. She hadn't seen him since that incident at the grill a couple nights ago and she wondered if her words made any kind of an impact. Caroline wasn't sure why she was hoping it did. Maybe she was just sick of seeing him look like a puppy who's been kicked in the legs whenever Elena walked by.

"Oh my god. I love pictionary!" Jenna yelled excitedly, stumbling in the direction of the main room and thus, leading the crowd with her.

~§~

Dropping her head to the table top, Caroline released a loud groan. That certainly sounded like a break up to her and although she knew that she should be celebrating the progress of her plan, she still felt horrible. They were her friends. The only people Caroline actually had and she was purposely trying to cause them pain. The only thing that got her through every desperate stunt she pulled today was the fact that they'd both be in more pain if Katherine started killing off family members.

"So, it looks like there's trouble in paradise." Squeezing her eyes closed, Caroline prayed that if she didn't look up or acknowledge Damon's presence that maybe he'd just go away. Only the whole idea of him disappearing due to lack of attention was shot out of the water when she sensed him sit down across from her.

"Better swoop in while she's questioning and vulnerable. Maybe you can get your next fix in before they patch things back up again." Finally drawing her head off the wooden table, she looked at him expectantly. Waiting for him to stand back up and go running. That's what he does right?

"Harsh, Blondie. And here I was think we were on the same side. What's your angle?" Carolines brows furrowed in confusion, trying to figure out what he was trying to imply.

"What the hell are you talking about?" She asked bluntly, not really feeling like playing around with him today. 'On the same side' means he wants something and thinks she wants the same thing. Better to just have him get on with it.

"Stefan and Elena? I heard you out on the porch today. 'Oh, Elena. Don't you know how much pain you're putting Stefan through by being in the same room as him?'" Caroline glared at his very off-key tone which sounded absolutely _nothing_ like her, thank you very much. "If Stefan was going go 'rip out her jugular' he would have done it by now. So what are you trying to accomplish? Trying to break them up so you can have a shot at Stefan yourself?" Caroline couldn't help but laugh at his accusation, which caused that know it all smirk to drop from Damon's features. She wished that was her reasoning. She wished things were that simple.

"You caught me, Damon. I decided to jump start a heart break for my own selfish gain. Who cares that they're my best friends? If they're broken up I might have a shot at the white knight. I'm sure he'll get over his epic love for Elena and fall straight into my arms in a matter of days." Swirling the straw around in her drink, Caroline didn't even bother to spare him another glance as she spoke in the heavy sarcasm. She was sure his next words would have been for them to team up. Have her go after Stefan so he has a chance at Elena. She should have guessed that her words the other night had no effect on him. "Are we done now?"

"No. Because then it just doesn't make any sense. Why do you want them to break up so badly if it's not to mend Stefan's broken heart?" His tone was laced in confusion as though he was scrambling for what her secret plan must be. In a way she almost felt bad for him.

"Did you ever think that maybe I just meant what I said? That I wanted Elena to completely understand the situation she's in? Not everyone has a master plan, Damon. We're not all out for ourselves." Slipping out of the booth, Caroline decided that this was a good enough time as any to leave. The less time she had to spend in Damon's company the better. Making a bee line for the door, she made it as far as a couple steps before something grabbed her from behind. Grabbing hold of her arms and slamming her up against the brick wall on the side of the building. Caroline was about to knee the attacker in the balls before she registered Damon's face sneering down at her.

"See, I just don't believe that Caroline. Being selfish is a part of who you are. I'm right, aren't I? You want Stefan. You don't care if he's hurt as long as he's not with Elena." She was struggling against his hold, trying to push him away from her but it was no use. Damon was stronger than her, a more experienced fighter. She didn't stand a chance.

"You're an idiot, you know that? A god damn fucking idiot. Don't you get it?" Caroline growled out in frustration, this time actually managing to force him into taking a step back, giving her an inch or two to breathe. "Katherine's going to _kill_ them. She's going to kill Elena and every single one of us if we don't do what she wants. But she'll only do that after she kills everyone else we care about and forces us to watch. And I know _you_ don't care about anyone besides yourself and Elena. But _I_ do. They can put the epic romance on hold for a couple days until we find a way to get rid of her. There's no reason for us to be having to clean up a bloodbath over a tempertantrum."

Caroline left off the part about Katherine coming to her, not only would Damon not care, but she didn't need everyone knowing about it. That would only lead to Katherine finding herself another spy. Her teeth were clenched tightly together as she stared Damon down, his gaze searching hers until finally he let her go, taking another step back but still not providing her with enough room to pull away from the wall.

"Since when does Katherine care enough about Stefan to come out of hiding and try to force a break up like a middle schooler?" She was thankful that at least Damon was onto the same thing she was. Although Katherine kept claiming to be here for Stefan, and Caroline could definitely see some real feeling in there, that wasn't enough of a reason to expose herself.

"I think she wants something else. I think she's using this as a distraction for us to focus on while she goes after what she really came here for. But until we figure out what that is... Stefan and Elena have to play along and do what she says. The only way to get a shot at her is if she thinks everything's going according to plan." Caroline states simply, rubbing her hands down the front of her jeans in an effort to clean off the dirt from the alleyway.

"So why not just tell Stefan and Elena that?" Damon questioned, but she could see the wheels turning in his head. Damon was smart and clever when he put his mind to it, he was used to going about his evil masterminded plans without alerting the others as to what the plan actually was. One step ahead. It was something she shared with him and apparently with Katherine as well. And Stefan and Elena lacked the ability.

"They can't pull it off. Have you seen their acting skills? They don't want to admit they're out matched until someone suffers for it and it's drilled into their heads. I'm not entirely convinced of how much truth was in that fight we overheard to begin with. That's a little too snappy for Elena. Especially an Elena who spend all day yabbering on about how worried she was for him. The two of them aren't going to be able to out play a player with Katherine's skill. They need a little reality push."

As she spoke Damon eyed the blonde in front of him in curiosity. It made sense, it was probably a much better plan than his original one of antagonizing and ignoring Katherine until she spilt the beans.

He knew Caroline was capable of the thinking, she was so useful to him when she was human because she was gifted in getting her nose into places it didn't belong. She was a planner and a schemer, just like he was. Just like Katherine was. He's just never met one that was doing it out of pure selflessness. She cared about these people so she didn't want them to die. It was a motive sure, but it was one of loyalty. And from his experience that wasn't commonly found.

"So you're pushing them to break up because you want to keep the body count down? Who are you and what have you done to Caroline?" He couldn't grasp it. With what he knew about Caroline, being after Stefan would have made more sense.

"I'm sorry, did you know her? I don't recall much of you ever taking the time to figure her out." Caroline snapped, folding her arms across her chest as she glared. She wasn't exactly in the best state of mind right now and dealing with thoughts of their past wasn't exactly helping her out.

"I'd say I found a few useful things out. If I remember correctly she really liked it when I did _this_" Caroline didn't realize he was advancing on her until his lips brushed against the sensitive flesh of her neck, managing to suck lightly on the skin over her pulse point which caused a light gasp to escape. It took her a second to regain enough of her brain power to push him away, narrowing her eyes at that stupid fucking smirk on his face.

"Don't touch me. I told you what you wanted to know so leave me alone." Feeling slightly more confident, she pushed off the wall and endeavored to move passed him. Now she was going to need a cold shower and something to make her lose her memory of the night. Possibly another drink.

"You wound me, Caroline. Why can't we be friends again?" His voice was light and almost cheery, which prompted her to grit her teeth in annoyance.

"Because I don't like you and we were never friends."

"Oh, come on. It wasn't _all_ bad. It's not like you weren't enjoying yourself for the most part." Turning back around to face him, Caroline took note of the wild look in his eye. As if he was reminiscing on just how much she 'enjoyed' it.

"You're disgusting. You messed with my head. I don't care how good the sex was or wasn't, it'll never be able to make up for that." Something flashed in Damon's eyes and for a second, she braced herself for an arrogant tangent about how well he knew the sex was or something of the sort. Maybe he'd just roll his eyes and walk away. At least then she could head home and crawl into bed. She was absolutely exhausted.

"How about a sincere, full hearted apology?" Caroline shot him a look of disbelief and although he didn't look to be joking, she wasn't about to take it seriously.

"Not even if you meant it. And it certainly would take more than that." She quipped, turning back around and walking out onto the sidewalk. Caroline had a while to go until she made it home and she definitely did not want to run into Katherine along the way.

"Would offering you a ride home be a good start?" Damon hadn't moved from his spot in the dark alley, Caroline could tell that from how far away his voice sounded. Releasing a sigh, she felt a bit of the wall of hatred break away. If they were both going to live in the same town, she figured they should at least be able to stand being in each other's presence.

"Fine. But only because I'm really not looking forward to walking. I shouldn't have sacrificed my car in the war against mega-bitch." Caroline couldn't help but smile at the sound of Damon's gruff laughter as he moved in front of her and led the way towards the pale blue camero in the distance.

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**A/N** **- Annnnnnd they can stand each other's existence. I'd call that progress. I created a past Caroline/Mason friendship because this story is going to have a lot of Caroline's background that we never really got in the show.**

**Reviews would be appreciated.**


	3. For a Pessimist, I'm Pretty Optimistic

**A/N - Happy Friday, everyone! This chapter is working off of 'Kill Or Be Killed' although the plot for this episode has been cut into two chapters mostly because fitting it all into one would have been ridiculously long. **

** Thank you so much for the reviews, favorites, and alerts! I really did not imagine that this many people would be interested in my story. **

**I'm also taking the time to answer a few of your guys questions. ~**

**1) A lot of you commented about Caroline and Damon's 'friendship' and not wanting it to happen too fast and everything. The past chapter did not mean, in any way shape or form, that the two of them are now all buddy-buddy. They're both still convinced that the other is the most annoying thing on the face of the planet. They're not about to become 'besties' anytime soon. **

**2) Damon/Caroline/Mason love triangle questions - I'm not a fan of love triangles. Personally I don't like the fact that someone has to walk away unhappy and heart broken. So no, that wasn't really the angle I was going for. But this doesn't mean that Damon won't get jealous over her friendship with Mason or any other males in the future. **

**3) Someone commented about not wanting me to make Damon look 'pathetic' and I just wanted to point out that I'm trying to write these characters true to the ones we saw on the show season two. I believe with a ship like Daroline that neither one of them have to change who they are in order to be together or make some crazy ass relationship work out. Turning Damon into a complete sap or whatever was meant by the word 'pathetic' is not and never will be my intention. I love his character the way it is. **

**Hope that cleared some things up for you all and happy reading!**

**Disclaimer: Don't own The Vampire Diaries or any of their characters. No matter how much I wish I did**.

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_"Optimism doesn't wait on facts. It deals with prospects. Pessimism is a waste of time."_

_- Norman Cousins_

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There was something about parents that made it so no matter how many times they disappointed you or let you down, you could never fully give up on them. Which is why Caroline, despite her better knowledge, was actually allowing herself to feel excited about this 'historical society volunteer day' whatever thing.

The only problem was that her mother was starting to sense something off with her. Caroline could tell and it was beginning to concern her. She still had a ways to go with living here and making sure Liz never found out that she was a vampire. As much as she wanted to believe that her mom would understand since it was _her daughter_ she knew better than to think that. Sheriff Liz Forbes was all work, all the time. That's how she functioned. It was also why Caroline couldn't help but be a little happy when her mother said she wanted to go to this event to spend the day with her. Caroline couldn't remember the last time mom chose her over work.

Twirling around in the full length mirror, Caroline flashed a large grin and straightened out her jacket. This was going to be a good day. She was going to make sure that it ran smoothly with no deaths or drama or any other Mystic Falls specialty. Deciding to just walk to the event to get a little peace of mind, Caroline left her bag with her car keys on the kitchen counter, grabbing an apple from the bowl on her way out the door.

It was a beautiful day in Mystic Falls, there was no doubt about it. It was nice and sunny, everyone was out on the side walks and in the streets talking and laughing, and Caroline was suddenly very thankful of the glistening blue ring on her finger that allowed her to be out on a day like today.

Munching on the juicy red fruit in her hand, she held her hand up in a wave as Mason drove by in that beat up truck of his. He didn't glance her way, instead focusing on the road ahead of him like he was off to set it on fire which only managed to confuse her. Mason was the typical 'surfer dude' he was never really upset or angry about anything. Everything just rolled off his back like the tide so with his destination looking to be the same as hers, Caroline wondered if her good day was actually going to last.

When the truck disappeared from view, she shook herself out of the negative feeling. _Positive thinking, Caroline. We have to stay optimistic_. Any day could be a good one if you make it that way. It was a saying she tried to live by.

Stepping onto the grass yard, Caroline looked around the area to see if she could spot anyone she knew. Everything was set up rather nicely, in her opinion. Although it looked boring for the younger generation who were running around playing tag, but Caroline figured there wasn't much you could do with a historical event in the way of children. Or teenagers either come to think of it.

She spotted her mother talking to Mrs. Lockwood and absentmindedly made her way in that direction. Seeing her made Caroline's mind travel back towards that whole 'werewolf' thing Elena told her about the other night and she wondered if Tyler and Mason were really _werewolves_. Wouldn't she know if they were? Or if the old mayor was? Wouldn't _somebody?_ Or was it really that easy to chalk it all up to ignorance?

"Hey, Mom. Mayor Lockwood." Caroline greeted as she approached the pair, effectively interrupting their whispered tones. Whispering was never a good sign, her mother was generally loud about everything. So Caroline could only take the low voices as something supernatural related and she so did not want to deal with any problems today. When she didn't get a response apart from nervous eye exchanges, Caroline fought the urge to roll her eyes and instead played oblivious. A skill she had perfected over the years. "Right. I was about to go grab some Lemonade."

Without waiting for an response, Caroline turned on her heel and headed away from her mother. Alright so that was the second act of bitchiness towards her mother today but she couldn't help it. First this morning she was getting too close to figuring out the Katherine thing and now she's trying to be motherly yet going back on her word an hour later?

She never actually made it to the lemonade drinking part of the day though because soon enough Elena came at her with a bombard of painting stuff. Elena. Right. She couldn't have a free day could she? There was still a job to be done.

"Want to help me start the painting?" Elena asked, it was like she was trying too hard to look happy when in reality she was barely keeping it together. Nodding her head with an overly bright smile, Caroline took some one of the brushes and paint containers and walked with her friend.

Starting up a conversation about her mother, she figured that she could at least get some ranting in before bringing up their relationship. She didn't want to seem obvious and honestly, talking about herself was something Elena would expect. Although pretty soon it became obvious Elena couldn't care less about Liz Forbes trying to become mother of the year so she finally brought up the Stefan topic.

As Elena talked Caroline felt the nervousness build up in the pit of her stomach again. Was she ever going to be able to do this without feeling so horrible about herself? She knew it needed to be done but that didn't make her feel less guilty. Caroline released a defeated sigh as Elena announced that she was going to talk to Stefan and walked over to him. If they were really fighting with each other, it wasn't going to be long before they made up. And if they were actually clever enough to try and stage this... It was a dangerous ground they just shouldn't be walking down.

"What's her problem?" Glancing to her side, Caroline withheld a groan when she caught sight of Damon. It was just like him to act like whatever that thing was last night didn't happen. Apparently if she was expecting any signs of a budding friendship on his part, she was going to be disappointed.

"Don't worry about it." Caroline mumbled, her thoughts elsewhere on how she was expected to keep the star crossed lovers apart _and_ keep her mother at bay at the same time...

"And why are you being such a bitch to your mom?" Snapping her head in his direction, Caroline couldn't help but scoff. That's right, Damon and her mother were 'friends', of course he'd blame her for the incidents this morning because that's what her mother always did.

"Don't worry about it." She repeated with more bite to her tone, moving away from him and picking up the previously discarded brush. Elena and Stefan were starting to argue and she tuned into the fight, trying to hear what was going on.

"I think you're right." Damon whispered in her ear, causing her to jump and almost drop the paintbrush. He was leaning over her, trying to give off the illusion that he was actually helping her, and she had to take in an unsteady breath when she felt the warmth of his body against her back. "If Stefan was going to give up, he would have already."

Drawing her lower lip between her teeth, Caroline tried to ignore the shiver his mouth against her ear sent through her body. Why was she suddenly so effected by his close proximity? What was wrong with her? Maybe it was just to be expected... Wouldn't anyone react this way with someone pressed up against them and whispering in their ear?

"That's what's concerning me." Caroline finally managed to say in response, thankful that she found her voice again. After an over exaggerated breaking of the fighting pair, Damon spoke louder than before.

"Relationships are about communication." She was confused at first until she saw Stefan look in their direction again, and she snorted and went to move away from Damon. He was making it known that they were listening. Maybe she should find Elena and see if she was okay.

Unfortunately, she didn't get far until there was a hand on her arm, turning her body back around and dragging it off towards the trees. "Damon, what the hell are you doing?" Caroline hissed, trying to pull her arm out of his grip and only managing to do so when he stopped moving. Looking around her she realized they were just far enough away from everyone else to ensure that they couldn't hear. "What is it?"

"How well do you know Mason Lockwood? Better than the rest of us from what it seemed like the other night." His voice was colder and more detached and Caroline got the idea that he meant business. She just didn't understand what Mason had to do with anything.

"I don't know him as well as I used too. Obviously, since he moved. Why?" She couldn't keep the curiosity out of her voice. If he was expecting her to help him with something Mason related, he was going to have to tell her why.

"Because he's trying to kill me. And he might go after Stefan too." Nodding her head as his answer sunk in, she tilted her head to the side in question.

"And why does he want to kill you? What'd you do to him?" Damon shot her a glare that showed how unhappy he was with her assuming that it was his fault but she only raised both of her brows expectantly.

"Always want to play me out as the bad guy, don't you? I might have possibly attempted to kill him. _Attempted_ being the key word. Werewolves are such grudge holders." Damon spoke so nonchalantly that Caroline couldn't help but drop her jaw in shock.

"What's with you and trying to kill everyone? We don't have to make everyone an enemy, Damon!" Her hand shot forward before she could stop it, the back of it hitting him square in the chest as she realized they now had yet another problem on their already huge list of problems.

"It's kill or be killed, Blondie. Now why would he go talking to your mother right after Stefan tried to negotiate peace with him?"

"You said 'tried'. Did he not accept the peace treaty?" That wasn't like Mason. He never involved himself in a conflict first. He was cool and collected until someone else threw the starting punch.

"Of course not. I stabbed him in the gut the night before with a knife. Luckily enough, Stefan reminded him of our numbers compared to his and I don't think he's stupid enough to try anything now." Blinking, Caroline let this sink in for a minute. So Stefan threatened Mason too?

"Damon. What would you do if you were out numbered and out strengthed?" Azure eyes narrowed in her direction but Caroline could definitely see the brains working behind them.

"Give up?" He tried hopefully, although both of them knew Damon wasn't one for backing down from a fight.

"Wrong. You'd find someone who could out number and out strength them."

"You're losing me, Caroline. How is your mother stronger than I am?"

"Uh... Because she's on a council with a bunch of other vampire killers? Which Mason would know about since he was the mayor's brother..." She trailed off, not needing to finish where she was going with this before Damon caught on.

"You're saying Mason knows about the council?" Rolling her eyes, Caroline shoved at his shoulder and she went to walk by him. She had to check in on Elena.

"Of course he knows! What I would really be worried about is whether he was smart enough to think of exposing you to it."

"Crap - Wait. Where are you going?"

"To talk to Mason and persuade him to leave you idiots alone." Speaking as though this should have been obvious, Damon's voice rose as he called after the retreating blonde but she simply ignored him. Like she didn't have enough worries about making sure Katherine doesn't start killing people off, including herself, she now had to overthink on Damon's issue.

After wandering around for a good ten minutes, Caroline finally spotted Mason chopping at some large pieces of wood. Quickening her steps, she hurried towards him even though she didn't have a clue what she was going to say. How was she supposed to keep them off Stefan and Damon's case without revealing that she was one of them?

"Mason!" Caroline called from behind him, watching as the older Lockwood focused on her and then broke out into a smile.

"Why am I not surprised that you're not doing any kind of work?" His tone was teasing and Caroline couldn't help but be grateful about the fact that she wasn't suspected as being supernatural.

"Because you know me better than that, Lockwood." She responded with a slight shrug of her shoulders, sitting down right on the tree stump he was using as a base to chop the wood on, basically enabling him from further work. "And I know you. Which means that I'm fully aware that Mason Lockwood wouldn't stick around this town for any longer than he has too. The funerals over and you met up with a couple old friends. You should be high tailing it out of here. What gives?"

In all honesty, Caroline had no idea what was going to come out of her mouth until she started talking, the words spilling out and making her realize that it actually made sense. What _was_ Mason still doing here anyway?

"Maybe I just missed it here. Missed being around my family. I just lost my brother, Caroline. Why wouldn't I want to be with them?" Caroline narrowed her eyes at the man before her, of course it made sense, but she knew this guy. That was too rehearsed, he wouldn't even make eye contact with her as he spoke it.

"Uh... because you hate it here? You're just like me with the constant want to leave but the only difference is that you actually can. Plus you're also a shitty liar, want to try again?" Resting her elbows onto her knees, she peered up at him waiting for some form of response. Caroline liked to blame it on curiosity but she thinks that she just has a real passion for meddling.

Running his hands over his face, Mason looked down at the persistent girl with a defeated groan. "What about if I told you it was for a girl?" Instantly, Caroline's entire face lit up, excitement clearly visible in wide crystal orbs.

"A _girl?_ Oh, now we're getting somewhere. Who is it? Does she live here or something?" She had to stop herself from firing off more questions as she hopped in place on the thick stump.

"No... No, she's not here. I - uh - I'm trying to find something for her. Like a family artifact to give to her, you know? Kind of like how people propose with an engagement ring that's been passed down through generations... Only I'm not talking about a ring."

Suddenly, a plan brewed in Caroline's mind. Making a deal with someone was all about two parties both getting what they want right? "Well... What if I offer you up a deal?"

Mason's eyes clouded with confusion as his head tilted to the side slightly. "What kind of deal? What are you talking about?"

"Well I know you're on the warpath for the Salvatore brothers... Don't look at me like that, do you really think this town could keep a secret like _that_ from _me?_ You know how nosy I am. So what if I help you find this artifact whatever thing for your girl and in return you leave them alone?" The smile on Caroline's face grew bigger, glad that she actually came up with something that might work.

"What - You know? About what they are?" Mason was absolutely dumbfounded, still not able to get over the fact that this young girl, well he guessed she wasn't that young anymore, was exposed to these monsters a general basis. And _knew_ it. "You know what they are and you're befriending them? What the hell is wrong with you?"

"They're not that bad. I mean Damon can be a dick at times but all these recent animal attacks and everything? That's not them. They actually help to protect the town. Stefan's actually a really close friend of mine."

"Does your mother know that you know about vampires?" Mason asked, causing Caroline to sigh. Why couldn't he just... Accept the deal so she could get on with the rest of the days scheming?

"No. And you can't tell her. I only found out myself because of Stefan. He told Elena because he's in love with her. Now can we get back to the topic at hand? Why don't you just leave them alone?"

"Because Damon tried to kill me, Caroline!" Mason whispered yelled, not wanting to alert any surrounding people of their conversational topic. "And Stefan threatened me in his brothers defense."

"They're brothers. Obviously they're going to protect each other. And like I said, they protect the town. You're new and could pose a threat. So this artifact..." Waving her hand in front of her, Caroline gestured for him to continue. Wondering what it was he was searching for anyway.

"I'm a Lockwood and I can't find it in my own house. What makes you think you could?" Caroline just stared at him. Was he serious?

"Because I'm Caroline Forbes? Who could get her nose into anything that she's not supposed too? Give me a few hours alone in that house and if it's there, you know I'll find it." She could tell Mason was thinking over her words, she did have a knack for figuring things out. She always found others lost objects, always won at hide and seek, always dug out the latest gossip. There wasn't a secret in Mystic Falls that Caroline didn't know, at least not any worth while ones.

"Alright. From here on out I won't put anymore effort into having them killed or picking a fight. But you have to help me out with this so I can get the hell out of this town." Wearing an overly smug grin, Caroline nodded her head in agreement. Sounded good to her.

"Deal. Call me whenever you want to go searching or whatever and I'll help you out." Jumping off the tree stump and turning away from him, Caroline mentally crossed 'dealing with Lockwood' off her list of things to do today.

"Hey, Caroline! It's called a moonstone. And I think Tyler might have a clue where it is. But you can't tell anyone, alright?" A moonstone? What the hell is that? Shooting a thumbs up in Mason's direction, Caroline broke out into a jog, knowing that she needed to find Elena in order to give Katherine some kind of report.

Thankfully it only took her a few minutes to find Elena, who was sitting on a large flat rock overlooking a small stream. Taking a deep breath, Caroline sat down beside her. "Are you okay?" She questioned in greeting, looking over at her friend. Where was her bitch streak when she needed it? It used to be easy to be bitter towards Elena but now... Caroline accepted the fact that if there was a running list of who to keep alive, she would be at the bottom of it and Elena would be at the top. But being the one who's always chosen wasn't Elena's fault - it was just the way it was.

"No." Elena replied simply, continuing to rip apart some small plant and tossing the pieces into the flowing water.

"Well, maybe it's for the best?" Caroline tried, going for optimism and hoping it played out well.

"It's not for the best Caroline, none of this is for the best." Elena responded in a bitchy tone that honestly almost matched hers. Sometimes it was easy to forget that Elena could have a bit of fire if she chose too. Caroline couldn't help but sigh. Elena worked on a different wave length than she did, in a lot of ways Elena was the most selfless person she knew. But other times, Elena tended to be selfish with the ones she loved. She was afraid to lose them.

"I'm sorry, okay? I don't mean to take it out on you. You're just being a good friend." The bitterness in Elena's tone was unmistakable and Caroline was instantly hit with a truck load of guilt. And on top of that she was about ninety-nine percent sure Elena _knew_ about her and Katherine.

"No I'm not. I'm not being a good friend at all." Truthfully, Caroline was this close to just spilling everything. Regardless of if Katherine was close by and listening. That was until she saw her mother crossing the parking lot with her phone. "Is she leaving?" A part of her was thinking that of course she was, that's what her mother always did. But the rest of her had a really bad feeling.

"Where is my mom going?" Talking more to herself than she was to Elena, Caroline scrambled to her feet and headed towards her mother, setting the conversation with Elena on the back burner as she approached the clearly emotionally turmoiled sheriff. "What's wrong?"

"Oh, nothing. I-a have something -"

"You mean work?" Caroline asked, cutting her mother off mid excuse. "I mean, you surprised me. You lasted more than five minutes." It was like bitch just rolled off her in the presence of her mother but she couldn't help the underlying resentment. Caroline had thought that maybe things would be different this time.

"It's important." Liz tried to reason with her daughter, clearly hoping this would be enough.

"It always is." Caroline retorted, folding her arms over her chest.

"I'm sorry." And just like that, her mother was walking away from her. Leaving her with flashbacks of the millions of other times in her life she's had to watch her mother leave.

And then she remembered her talk with Damon. Him complaining about Mason talking with her mother and the reason she had to strike a deal with him in the first place. What if she was too late?

_From here on out_...

"Shit! Something's wrong. We have to find Stefan and Damon." Caroline voiced aloud to Elena, turning away and making a mad dash for the woods.

* * *

**A/N - Hope you guys enjoyed. Feel free to ask questions and I'll respond like I did in the beginning of this chapter. Review please. **


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